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Epin and Boronic Esters Designed and Manufactured by abcr service lab abcr service lab M a d e in Germ a n y Boronic acids and their esters are long-known reagents especially useful in Suzuki-Miyaura cross-coupling reactions. One of the disadvantages of these compounds is their limited hydrolytic stability during chromatographic purification. Introduction of a new class of boronic esters with enhanced stability provided by the 3,4-diethyl-hexane-3,4-diol (Epin) fragment allows one to overcome these limitations [1]. Therefore we present the diol precursor Epin, the respective diboronate (BEpin)2 and boronic acid esters as commercially available building blocks for different reactions. Benefits of Epin-derived boronic reagents: ■ Higher yields and less side products in cross-coupling reactions compared to generally used boronic esters ■ High stereoselective impact on asymmetric reactions due to the Epin-substituent [2,3] ■ Chromatographic stability of boronic esters with various functional groups abcr offers both Epin and (BEpin)2 as precursors of Epin-boronates. These two complementary reagents open a versatile toolbox leading towards the generation of boronic acid derivatives via e.g. condensation or coupling. Ar B Ar B O O O O Et Et Et Et Me Me Me Me Ar B OH OH Ar = Aryl or Heteroaryl increasing stability on silica gel & increasing yields in Suzuki-Miyaura cross-coupling reactions Et Et HO Et Et OH Epin Et Et Et Et Et Et Et Et O O B B O O (BEpin)2 Suzuki-Miyaura cross-coupling Ar Ar' Ar B O O Et Et Et Et Ar = Aryl or Heteroaryl Having the know-how of production of the above mentioned materials, abcr can also offer custom synthesis of a broad variety of boronic acid Epin esters for R&D purposes. Gute Chemie 3 2 - . . 1 2 2 0 1 5 5 1 3 8 5
Examples of Epin and Boronic Esters Designed and Manufactured by abcr service lab Et Et Et Et HO OH Et Et Et Et O O B B O O Et Et Et Et B(Epin) MeO B(Epin) N Epin AB582771 (BEpin)2 AB582939 3-(BEpin)-pyridine AB582940 3-(BEpin)-anisole AB583145 References [1] Oka et al. Org. Lett. 2022, 24, 3510-3514. [2] Incerti-Pradillos et al. Angew. Chem. Int. Ed. 2013, 52, 5338-5341. [3] Villar et al. Chem. Eur. J. 2018, 24, 16262-16265. abcr service lab: consultation, synthesis and optimization We offer customized individual syntheses for our customers. We know – there is no such thing as ready-made innovative chemical products off the rack. Our service for special chemicals fulfils complex tasks: ■ We comprehensively advise customers in regard to initial syntheses. ■ De-novo synthesis of exceptionally complex molecules and compounds for various industrial areas (such as pharma, material sciences, life science) ■ We optimize syntheses and advise our customers in order to discover efficient or cost-effective synthesis routes and thereby increase yields and purities. abcr’s internal state-of-the-art chemistry lab is available to our experts for any form of synthesis. Chemists with many years of experience and a scientific background from prior collaboration with worldwide renowned research institutes work here. Take advantage of the certified abcr know-how and our longstanding expertise. We are your service provider for individual syntheses – sales@abcr.com Gute Chemie abcr GmbH ▪ Phone +49 721 95061 - 0 ▪ Fax +49 721 95061 - 80 ▪ info@abcr.com ▪ www.abcr.com